A beach with red and beige umbrellas, white and red beach chairs, and rocky outcrops.

Dickinson Holiday Rentals

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Our top choices for Dickinson holiday rentals

1. Dickinson Bayou Front Retreat Gateway Spacious 5-bedroom with Water view fishing

Dickinson Bayou Front Retreat Gateway Spacious 5-bedroom with Water view fishing
Dickinson
9.0 out of 10, Wonderful, (12 reviews)
"View was great! The house was well equipped with everything we needed with lots of extra towels and linens. Very comfortable stay for our group of 10 adults."
United States
Rebecca E.
The price is NZ$754
includes taxes & fees
14 Sept - 15 Sept
Dickinson Bayou Front Retreat Gateway Spacious 5-bedroom with Water view fishing

2. Spacious 3BR/2BA Home Near Galveston Cruise Port, NASA & Houston

Spacious 3BR/2BA Home Near Galveston Cruise Port, NASA & Houston
Dickinson
8.4 out of 10, Very good, (21 reviews)
"Clean, spacious for a family group of 9. Perfect location for a stop-over on our way to Galveston for a cruise."
United States
James P.
The price is NZ$582
includes taxes & fees
14 Sept - 15 Sept
Spacious 3BR/2BA Home Near Galveston Cruise Port, NASA & Houston

3. Waterfront Retreat Getaway with Gameroom Firepit Fishing Kayaks

Waterfront Retreat Getaway with Gameroom Firepit Fishing Kayaks
Dickinson
8.0 out of 10, Very good, (3 reviews)
"The house was very clean and comfortable! The master bed was very comfy. The only thing that was weird was there were no dressers. But that didn’t really affect us. Kids loved all the extra stuff and we loved staying right on the water. My husband enjoyed fishing and catching a few things. Nothing big, but at least he was able to fish on vacation. "
United States
Alvie May F.
The price is NZ$696
includes taxes & fees
17 Aug - 18 Aug
Waterfront Retreat Getaway with Gameroom Firepit Fishing Kayaks

4. Waterfront Oasis with Pool, Fire Pit & Dock

Waterfront Oasis with Pool, Fire Pit & Dock
Kemah Area
7.0 out of 10, Good, (10 reviews)
"This property had every amenity for entertainment "
United States
Ali T.
The price is NZ$1,279
includes taxes & fees
19 Aug - 20 Aug
Waterfront Oasis with Pool, Fire Pit & Dock

5. Private Mansion Retreat Basketball Court and More

Private Mansion Retreat Basketball Court and More
2.0 star property
Dickinson
The price is NZ$4,753
includes taxes & fees
23 Aug - 24 Aug
Private Mansion Retreat Basketball Court and More

6. Luxe Villa Close to Galveston, Kemah, NASA & Houston

Luxe Villa Close to Galveston, Kemah, NASA & Houston
Dickinson
The price is NZ$1,017
includes taxes & fees
24 Aug - 25 Aug
Luxe Villa Close to Galveston, Kemah, NASA & Houston

7. Charming 2-bedroom cabin with WiFi, AC in tranquil surrounding.

Charming 2-bedroom cabin with WiFi, AC in tranquil surrounding.
San Leon
8.6 out of 10, Excellent, (7 reviews)
"Clean rooms had everything we need for the stay"
United States
G
The price is NZ$261
includes taxes & fees
23 Aug - 24 Aug
Charming 2-bedroom cabin with WiFi, AC in tranquil surrounding.

8. 2-bedroom 2 bath..4 beds total Amazing Waterfront condo w/310 ft lit pier

2-bedroom 2 bath..4 beds total Amazing Waterfront condo w/310 ft lit pier
San Leon
10.0 out of 10, Exceptional, (1 review)
"The property is very comfortable and has all the amenities needed and then some. The kitchen is fully stocked, the appliances are first rate, and the furnishings are a great mix of modern and antiques. I felt like I was at home, not in a rental. The owner was very responsive to any questions I had while staying on the property. "
United States
Cindy B.
The price is NZ$859
includes taxes & fees
28 Aug - 29 Aug
2-bedroom 2 bath..4 beds total Amazing Waterfront condo w/310 ft lit pier

9. Waterfront Bay Views | Beautiful Private Pier

Waterfront Bay Views | Beautiful Private Pier
San Leon
10.0 out of 10, Exceptional, (24 reviews)
"Such a beautiful house and view! We would absolutely stay here again! Communication was excellent! Location was great! Quiet neighborhood!"
United States
Brittany P.
Waterfront Bay Views | Beautiful Private Pier

10. San Leon, Galv Bay- 300' Private Pier w/ Green Fishing Lights! Immaculate home!

San Leon, Galv Bay- 300' Private Pier w/ Green Fishing Lights! Immaculate home!
San Leon
10.0 out of 10, Exceptional, (9 reviews)
"Beautiful place !! We loved our stay "
United States
Yenly P.
The price is NZ$687
includes taxes & fees
13 Sept - 14 Sept
San Leon, Galv Bay- 300' Private Pier w/ Green Fishing Lights! Immaculate home!

11. Artistic & Charming 2-bedroom house on quiet lake near NASA and Galveston

Artistic & Charming 2-bedroom house on quiet lake near NASA and Galveston
San Leon
10.0 out of 10, Exceptional, (9 reviews)
"Outstanding overall stay. This property is excellent "
United States
annalicia v.
The price is NZ$672
includes taxes & fees
6 Sept - 7 Sept
Artistic & Charming 2-bedroom house on quiet lake near NASA and Galveston

12. Charming Cottage I on Dickinson Bay

Charming Cottage I on Dickinson Bay
San Leon
9.2 out of 10, Wonderful, (9 reviews)
"Everything was very good. Enjoy our stay "
United States
Richard N.
The price is NZ$423
includes taxes & fees
17 Aug - 18 Aug
Charming Cottage I on Dickinson Bay

13. Stunning Home with Expansive Pool & Game Room

Stunning Home with Expansive Pool & Game Room
San Leon
8.8 out of 10, Excellent, (49 reviews)
"Great property and great value. Host was very communicative and the check in process was seamless. The barn was the big hit with our family. Great place to hang out with plenty to do for the kids. Property is super close to the Kemah Boardwalk which is a must do if you are from out of town. "
United States
Jason W.
The price is NZ$592
includes taxes & fees
27 Aug - 28 Aug
Stunning Home with Expansive Pool & Game Room

14. Bay Breeze Bungalow - Game Room & Pet Friendly

Bay Breeze Bungalow - Game Room & Pet Friendly
San Leon
9.6 out of 10, Exceptional, (8 reviews)
"The property was close to family who live in the area and very accommodating for us. Host was super, always keeping us informed and checking on our needs. "
United States
Kathy B.
The price is NZ$647
includes taxes & fees
17 Aug - 18 Aug
Bay Breeze Bungalow - Game Room & Pet Friendly

15. Lakefront Escape | 3BD/2BA Guesthouse in San Leon

Lakefront Escape | 3BD/2BA Guesthouse in San Leon
San Leon
The price is NZ$656
includes taxes & fees
14 Sept - 15 Sept
Lakefront Escape | 3BD/2BA Guesthouse in San Leon

16. “Big Shirley” in Sunny San Leon

“Big Shirley” in Sunny San Leon
San Leon
10.0 out of 10, Exceptional, (2 reviews)
"Helpful owners"
United States
David
The price is NZ$334
includes taxes & fees
17 Aug - 18 Aug
“Big Shirley” in Sunny San Leon

17. Bella's Bungalow in Sunny San leon, TX. Come to escape and enjoy the Salt Life!

Bella's Bungalow in Sunny San leon, TX. Come to escape and enjoy the Salt Life!
San Leon
8.0 out of 10, Very good, (1 review)
"The dog next door barked a lot and we did not have any wash cloths or kitchen towels. Other than that the place was small but comfortable. Perfect for our short visit to the area. "
United States
Edith
The price is NZ$196
includes taxes & fees
17 Aug - 18 Aug
Bella's Bungalow in Sunny San leon, TX. Come to escape and enjoy the Salt Life!

18. Peaceful Retreat with Texas-Shaped Pool

Peaceful Retreat with Texas-Shaped Pool
San Leon
7.0 out of 10, Good, (2 reviews)
"Property is great for outside fun"
United States
Yuli h.
The price is NZ$678
includes taxes & fees
17 Aug - 18 Aug
Peaceful Retreat with Texas-Shaped Pool

19. Private Luxury Estate Retreat 8 Acres Near Galveston and Houston

Private Luxury Estate Retreat 8 Acres Near Galveston and Houston
Dickinson
The price is NZ$3,181
includes taxes & fees
17 Aug - 18 Aug
Private Luxury Estate Retreat 8 Acres Near Galveston and Houston
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Dickinson Hotel Reviews

Find out more about Dickinson

You always said you would go on a dream holiday someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannonball into the deep end. Go ahead, unplug and unwind in style. When you book one of our Dickinson holiday rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your holiday just got upgraded.

As much as you love your vacation rental, it’s always good to get out and explore to soak up Dickinson. Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in Dickinson. Seeing all the best attractions is bound to make you fall in love with Dickinson. Who knows, you may even be tempted to extend your stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true. 

It’s your escape so why share it? You deserve your own slice of paradise. Booking your holiday rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in Dickinson short-term rentals, that won’t be hard to do.

Frequently asked questions

Can I find a holiday rental in Dickinson?

Yes, there are holiday rentals in Dickinson close to Bay Area Raceway, or you can select a more secluded option if you're looking for a relaxing stay. Dickinson is known for its sporting events and shopping. Make sure you have time to check out the spas and restaurants during your trip.

What are some of the best holiday rentals that Dickinson has to offer?

Salty Suites, beachfront, hot tub: This holiday home rental outside of Dickinson offers a balcony, a garden and a BBQ to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a dishwasher, a fridge and a stovetop. You and your friends and family can relax into your holiday with amenities such as 1 hot tub.

How many holiday rentals will I find in Dickinson?

With 61 Expedia holiday rentals, you're guaranteed to find just the right place for your Dickinson stay.

What can I see and do in Dickinson?

Cultural attractions include Dickinson Historic Railroad Center, whereas Bay Area Raceway is just one of the family-friendly sights. Other popular places to visit in the area include Port of Galveston Cruise Terminal and Galveston Seawall.

What are holiday rentals like in Dickinson?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Dickinson. Holiday rentals offer extras like WiFi and washers and dryers so you'll be comfy for your stay. If you're concerned about a sanitised environment, holiday rentals can provide a sense of security away from shared hotel lifts and lobbies packed with people while still allowing you the excitement and enjoyment of travel. You'll also have more space in a holiday rental than in a traditional hotel, which makes a holiday rental a great choice for a family trip.